Sodium hydride → (S)-5,11-Dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine

HRID 1460490ノート

反応式

HRID 1460490 の反応式
[H-].[Na+].COC1C=CC(CCN2CCC[C@H]2C[N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][S:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=CC=1.[CH3:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:44]2[CH2:48][CH2:47][CH2:46][C@H:45]2[CH2:49]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:43])=[O:42])=[CH:37][CH:36]=1>CN(C)C=O>[CH3:34][C:35]1[CH:36]=[CH:37][C:38]([S:41]([N:44]2[CH2:48][CH2:47][CH2:46][C@H:45]2[CH2:49][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][S:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)(=[O:42])=[O:43])=[CH:39][CH:40]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepineHCID 10905672{(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl 4-methylbenzenesulfonate

生成物 1

HCID 22841645(S)-5,11-Dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine収率 24%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

Sodium hydride (80% dispersion in oil, 40 mg) was added to a solution of 5,11-dihydrodibenzo[b,e][1,4]thiazepine (see Example 1 for source) (213 mg) in dimethylformamide (10 ml) and the mixture heated at 60° C. for 45 minutes, treated with a solution of (S)-1-(4-methylphenylsulphonyl)-2-(4-methylphenylsulphonyloxymethyl)pyrrolidine (see Preparation 15 for source) (440 mg) in dimethylformamide (5 ml), heated at 60° C. for 7 hours and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, performing a gradient elution initially using hexane as eluant and changing to hexane/ethyl acetate (60:40). Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil, (50 mg, 24%).

後処理

  1. temperatureheated at 60° C. for 7 hours
  2. customevaporated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic layer washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. washa gradient elution initially using hexane as eluant
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-97893069a3d14070b840dee150605748
出典データセット
uspto-grants-1991_12
特許番号
US05071844

反応ノート

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